In the electrophilic aromatic substitution of pyrrole at the kinetically preferred C-2 position, how — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

When an electrophile attacks pyrrole at the C-2 position, the resulting positive charge can be delocalized across the adjacent carbon atoms and onto the nitrogen atom via its lone pair. This results in exactly 3 distinct resonance structures, compared to only 2 structures for attack at the C-3 position. The most stable of these 3 structures places the positive charge on the nitrogen atom, granting every atom a complete octet.